New England’s Great Barrington for Pumpkins

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For our annual pumpkin and apple festivities this year, we headed to Great Barrington, Massachusetts, which is about a three hour drive from New York City.

To Eat

We had a delicious meal at farm-to-table restaurant Prairie Whale. It was started by an ex-Brooklynite, and definitely has that hip, rustic vibe. The cornbread with jalapeno butter was a huge hit, as was the Cerdon sparkling rose (honestly, it was probably the best rose I’ve ever taste–reminded me of forest fruit from Sweden, complete with millions of tiny bubbles! I found it locally here in NYC at Astor Wines, if you want to give it a try!)

And, ever the fans of the Red Lion Inn, we went there for a delightful lunch, filled with warm soups, cheese plates, and Oktoberfest ales! The place is super cozy and basically screams fall with the giant pumpkins out front and fire roaring in the lobby.

To Do

Wanting to experience foliage, we were torn between a “gentle hike” up the mountain or a (much) gentler stroll around the Berkshire Botanical Garden…in the end we went with much gentler:-) And so very happy we did! The garden was small as gardens go (much smaller than the one in the Bronx, for comparison), but truly beautiful and curated. And the children’s garden was a true delight! There were stumps for jumping, pails for watering, shovels for digging, pumpkins for picking, and even a fairy garden for exploring! Augusten could have easily stayed the entire day.

We also spent time exploring the towns of Stockbridge and Great Barrington, popping into tiny shops filled with records, used books, locally made soaps, jewelry, crystals and stones, and tons of coffee.
Two that really stood out this time around were Rubiner’s for their fantastic selection of cheese and wine (pick some up for a cozy dinner back at the hotel!) and One Mercantile, for their yummy pumpkin scented candles, locally handmade greeting cards, and unique (and reasonably priced!) jewelry.

To Stay

We stayed at the Briarcliff Motel again, and again, were so pleased. The bonfire out front was so lovely to sit around in the evenings, and the hammocks out back were wonderful for mid-afternoon rests.

The rooms are all decked out in quirky 1960’s decor, and at a little over $100 a night, you just can’t go wrong. Oh! And, they paired up with the swanky Red Lion Inn right down the road, and you can now go and use their gym and outdoor heated pool, free of charge. A nice little perk!


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